Synthesis of Silylated Sugars
This project is centered on the synthesis of silylated compounds; mainly sugars. By employing trimethylsilane (TMS) as a protecting group for the hydroxyl of sugars, we are hoping to correlate the reactivity of said protecting groups with calculated electron densities. This correlation can be achieved through the use of (29)Si NMR, HMBC, HSQC, and COSY. In this way, we may find an explanation as to the order of reactivity of the TMS protecting groups, which has been observed through the use of ReSET (Regioselective Silyl Exchange Technology). In addition, the silylated compounds act as intermediates in the synthesis of more complex compounds which, in the future, will act as internal standards for mass spectrometry for the detection, isolation, and extraction of compounds of interest in tea. The compounds of interest are unavailable commercially due to their difficulty to synthesize. Because of this, we are examining ways of streamlining the synthesis of such compounds.
Links Related Research:
US Patent: Gervay-Hague J, Schombs M inventors. The Regents of the University of California (Oakland, CA), assignee. Regioselective Silyl Exchange of Per-Silylated Oligosaccharides. US 2016/0176909 A1.
Hsieh, Hsiao-Wu; Schombs, Matthew W.; Witschi, Mark A.; Gervay- Hague, Jacquelyn. Regioselective Silyl/Acetate Exchange of Disaccharides Yields Advanced Glycosyl Donor and Acceptor Precursors. Journal of Organic Chemistry. 2013, 78(19): 9677-9688. DOI: 10.1021/jo4013805
Park, Simon S., Gervay-Hague, J. “Synthesis of Partially O-Acetylated N-Acetylneuraminic Acid Using Regioselective Silyl Exchange Technology” Organic Letters. 2014, 10: 1021-1023. DOI: 10.1021/ol502389g
Hsieh, Hsiao-Wu; Schombs, Matthew W.; Gervay-Hague, Jacquelyn. Integrating ReSET with Glycosyl Iodide Glycosylation in Step- Economy Syntheses of Tumor-Associated Carbohydrate Antigens and Immunogenic Glycolipids. Journal of Organic Chemistry. 2014, 79(4): 1736-1748. DOI: 10.1021/jo402736g
Hsieh, Hsiao-Wu; Davis, Ryan A.; Hoch, Jessica A.; Gervay-Hague, Jacquelyn. Two-Step Functionalization of Oligosaccharides Using Glycosyl Iodide and Trimethylene Oxide and Its Applications to Multivalent Glycoconjugates. Chemistry – A European Journal. 2014, 20(21): 6444-6454. DOI: 10.1002/chem.201400024